I spent many years traveling for business, but I never had to “dress for travel” because I was always in business ensembles. Because of that experience, I continued to think carefully about what I wore for traveling when that part of my career ended. I always wanted to look sophisticated and well-dressed – like maybe I was still a road warrior.

As the years passed, I slowly changed my travel apparel to reflect two things: 1) the fact that most people were dressing down and I stuck out, and 2) the fact that I wanted and needed to be comfortable – you know, i case I had to spend the night on the floor in the airport or really run to catch a train.

Wear clothing that you plan to wear in some combination at your destination. If I wear leggings, I know they can double as exercise tights once I arrive. I will wear a duster sweater (bulky to pack) and then wear it later in my trip. This also presumes that I have picked a base color for my travel wardrobe of either black, navy, or a shade of brown.

Wear cute AND comfortable shoes. Nothing is worse than finding out that your shoes are uncomfortable halfway to your gate. I used to always wear a shoe with a heel (because I wanted to be taller than everyone else), but I have gradually shifted to certain low heels, cute flats, or sneakers.

Organize your clothing layers before you leave. Perhaps, like me, you fly from California to the East Coast in winter. I don’t need a coat on the front end but I’ll surely need one on the back end. So my winter coat is packed with gloves or mittens on the top of my bag for easy access after I land. Then there is the issue of staying warm and comfortable on the plane. I always carry a big scarf, an eye mask and earplugs.

Wear makeup and take the time to look nice! You never know who you’ll meet on the plane and don’t you ultimately just want to look better than everyone else you’re with?